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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:51:52 UTC
Update Date2022-03-07 02:54:39 UTC
HMDB IDHMDB0035841
Secondary Accession Numbers
  • HMDB35841
Metabolite Identification
Common NameCitronellal
DescriptionCitronellal, also known as 2,3-dihydrocitral or beta-citronellal, belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle. Based on a literature review a significant number of articles have been published on Citronellal.
Structure
Data?1563862780
Synonyms
ValueSource
2,3-DihydrocitralChEBI
3,7-Dimethyl-6-octen-1-alChEBI
3,7-Dimethyl-6-octenalChEBI
beta-CitronellalChEBI
b-CitronellalGenerator
Β-citronellalGenerator
3,7-Dimethyloct-6-enalHMDB
beta -CitronellalHMDB
FEMA 2307HMDB
RhodinalHMDB
Citronellal, (+-)-isomerMeSH, HMDB
Citronellal, (S)-isomerMeSH, HMDB
Citronellal, (R)-isomerMeSH, HMDB
Chemical FormulaC10H18O
Average Molecular Weight154.253
Monoisotopic Molecular Weight154.1357652
IUPAC Name3,7-dimethyloct-6-enal
Traditional Namecitronella
CAS Registry Number106-23-0
SMILES
CC(CCC=C(C)C)CC=O
InChI Identifier
InChI=1S/C10H18O/c1-9(2)5-4-6-10(3)7-8-11/h5,8,10H,4,6-7H2,1-3H3
InChI KeyNEHNMFOYXAPHSD-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentAcyclic monoterpenoids
Alternative Parents
Substituents
  • Acyclic monoterpenoid
  • Medium-chain aldehyde
  • Alpha-hydrogen aldehyde
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aldehyde
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point206.00 to 207.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility38.94 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP3.297 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.36 g/LALOGPS
logP3.25ALOGPS
logP2.71ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)18.32ChemAxon
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity49.3 m³·mol⁻¹ChemAxon
Polarizability19.18 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+137.33931661259
DarkChem[M-H]-133.62731661259
DeepCCS[M+H]+139.21730932474
DeepCCS[M-H]-135.63230932474
DeepCCS[M-2H]-172.87330932474
DeepCCS[M+Na]+148.11130932474
AllCCS[M+H]+137.732859911
AllCCS[M+H-H2O]+133.732859911
AllCCS[M+NH4]+141.532859911
AllCCS[M+Na]+142.632859911
AllCCS[M-H]-139.032859911
AllCCS[M+Na-2H]-141.032859911
AllCCS[M+HCOO]-143.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
CitronellalCC(CCC=C(C)C)CC=O1484.4Standard polar33892256
CitronellalCC(CCC=C(C)C)CC=O1116.8Standard non polar33892256
CitronellalCC(CCC=C(C)C)CC=O1154.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Citronellal,1TMS,isomer #1CC(C)=CCCC(C)C=CO[Si](C)(C)C1330.6Semi standard non polar33892256
Citronellal,1TMS,isomer #1CC(C)=CCCC(C)C=CO[Si](C)(C)C1294.0Standard non polar33892256
Citronellal,1TBDMS,isomer #1CC(C)=CCCC(C)C=CO[Si](C)(C)C(C)(C)C1548.0Semi standard non polar33892256
Citronellal,1TBDMS,isomer #1CC(C)=CCCC(C)C=CO[Si](C)(C)C(C)(C)C1518.1Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Citronellal EI-B (Non-derivatized)splash10-066v-9200000000-145d8f7001c4ce77fa8c2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Citronellal EI-B (Non-derivatized)splash10-066u-9100000000-95b49c5f5088a3eddc722017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Citronellal EI-B (Non-derivatized)splash10-066v-9200000000-145d8f7001c4ce77fa8c2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Citronellal EI-B (Non-derivatized)splash10-066u-9100000000-95b49c5f5088a3eddc722018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Citronellal GC-MS (Non-derivatized) - 70eV, Positivesplash10-000x-9400000000-61094362cba6ad2562d72017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Citronellal GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citronellal 10V, Positive-QTOFsplash10-0a4i-1900000000-facaeed6253aef58db1e2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citronellal 20V, Positive-QTOFsplash10-0aor-9700000000-246e147d68730886b9362016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citronellal 40V, Positive-QTOFsplash10-0ldl-9000000000-a497aaf732131b397f9b2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citronellal 10V, Negative-QTOFsplash10-0udi-0900000000-804231e21b402460f30f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citronellal 20V, Negative-QTOFsplash10-0udi-2900000000-e11d5a0124399999066a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citronellal 40V, Negative-QTOFsplash10-0006-9300000000-55b14a46099707c2eeb92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citronellal 10V, Positive-QTOFsplash10-05o3-9100000000-f88a67993a6d30f736f32021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citronellal 20V, Positive-QTOFsplash10-00lu-9000000000-069ce8d3e8f400ae43842021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citronellal 40V, Positive-QTOFsplash10-0006-9000000000-a86a178bcdeaecf8351d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citronellal 10V, Negative-QTOFsplash10-0udi-0900000000-d2363ae8d4dbdcccda802021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citronellal 20V, Negative-QTOFsplash10-0h90-0900000000-399caab2275c277c7c122021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citronellal 40V, Negative-QTOFsplash10-01tc-9000000000-4f5c5668195b4a69808e2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB014617
KNApSAcK IDC00035823
Chemspider ID7506
KEGG Compound IDC17384
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCitronellal
METLIN IDNot Available
PubChem Compound7794
PDB IDNot Available
ChEBI ID47856
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1032651
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.